Benzylidenemalononitrile

Base Information

• Chemical Name: Benzylidenemalononitrile
• CAS No.: 2700-22-3
• Molecular Formula: C10H6N2
• Molecular Weight: 154.171
• Hs Code.: 29269095
• European Community (EC) Number: 220-283-6
• NSC Number: 490
• UNII: 2HQB24UJ25
• DSSTox Substance ID: DTXSID10181490
• Nikkaji Number: J41.614B
• Wikidata: Q83052120
• Mol file: 2700-22-3.mol

Synonyms:Benzylidenemalononitrile;2-Benzylidenemalononitrile;2700-22-3;Benzalmalononitrile;Benzylidenemalonodinitrile;alpha-Cyanocinnamonitrile;Benzylidene malononitrile;MALONONITRILE, BENZYLIDENE-;2-benzylidenepropanedinitrile;Benzal-malonitril;beta,beta-Dicyanostyrene;2,2-Dicyano-1-phenylethylene;2-Phenyl-1,1-dicyanoethylene;Propanedinitrile, (phenylmethylene)-;2-(phenylmethylidene)propanedinitrile;beta,beta-Styrenedicarbonitrile;NSC 490;2-Benzylidene-malononitrile;Benzal-malonitril [German];AI3-19689;EINECS 220-283-6;F 2370;TL 237;.alpha.-Cyanocinnamonitrile;.beta.,.beta.-Dicyanostyrene;2HQB24UJ25;NSC-490;Propanedinitrile, 2-(phenylmethylene)-;benzylidenepropanedinitrile;Benzalmalonitrile;2-(phenylmethylene)Propanedinitrile;benzylidenemalonitrile;I+/--Cyanocinnamonitrile;WLN: NCYCN&1R;Malonodinitrile, benzylidene;UNII-2HQB24UJ25;2-Benzylidenemalononitrile #;SCHEMBL60843;(Phenylmethylene)malononitrile;1,1-Dicyano-2-phenylethene;2-Phenyl-1,1-dicyanoethene;2-benzylidene-propanedinitrile;2-Cyano-3-phenylacrylonitrile;Benzylidenemalononitrile, 98%;1,1-Dicyano-2-phenylethylene;NSC490;(Phenylmethylene)propanedinitrile;WAVNYPVYNSIHNC-UHFFFAOYSA-;DTXSID10181490;HMS1787C07;.beta.,.beta.-Styrenedicarbonitrile;MCK102227;MFCD00001855;STL139251;AKOS001012099;AS-58817;LS-88854;A5283;B0947;CS-0186558;FT-0622851;D88718;J-016644;Z44299997;F6782-3634

Chemical Property of Benzylidenemalononitrile

Chemical Property:

• Appearance/Colour: slightly yellow needle-like crystalline powder
• Vapor Pressure: 0.00159mmHg at 25°C
• Melting Point: 83-85 °C(lit.)
• Refractive Index: 1.612
• Boiling Point: 294.8 °C at 760 mmHg
• Flash Point: 138 °C
• PSA: 47.58000
• Density: 1.154 g/cm³
• LogP: 2.11716
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 154.053098200
• Heavy Atom Count: 12
• Complexity: 247

Purity/Quality:

97% ^*data from raw suppliers

2-Benzylidenemalononitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=C(C#N)C#N
• Uses: Benzylidenemalononitrile was used in fluorescence-based assay for determination of soluble methane monooxygenase activity in solution.

Technology Process of Benzylidenemalononitrile

There total 73 articles about Benzylidenemalononitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

benzaldehyde dimethyl acetal (1125-88-8) + malononitrile (109-77-3) → Benzylidenemalononitrile (2700-22-3)

Guidance literature:

With FeO_x, Al₂O_{3 and} ZrO₂ dispersed pyrogallic acid (PG)-assisted layer-by-layer coated hierarchically porous silica; In water; toluene; at 80 ℃; for 3h; Reagent/catalyst;

DOI:10.1039/c6ra12088a

Reference yield: 99.0%

malononitrile (109-77-3) + benzyl alcohol (100-51-6,185532-71-2) → Benzylidenemalononitrile (2700-22-3)

Guidance literature:

With oxygen; In toluene; at 100 ℃; for 13h; under 760.051 Torr; Reagent/catalyst; Solvent; Temperature;

DOI:10.1002/ejic.201500808

Reference yield: 99.0%

benzylidene phenylamine (538-51-2) + malononitrile (109-77-3) → Benzylidenemalononitrile (2700-22-3)

Guidance literature:

With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((1S,2R)-1-(piperidin-1-yl)-2,3-dihydro-1H-inden-2-yl)thiourea; In 5,5-dimethyl-1,3-cyclohexadiene; at 20 ℃; for 0.333333h; Molecular sieve;

DOI:10.1002/chem.201103136

upstream raw materials:

2-cyano-3-phenylacrylamide

2-benzylidenepropanediamide

sodium ethanolate

benzaldehyde

Downstream raw materials:

Benzyl-but-2-enyl-malononitril

2,2-dicyano-3-phenyl-propionic acid ethyl ester

2-benzyl-2-(4-nitrophenyl)malononitrile

4-Methyl-1-phenyl-2,2-dicyan-penten-⁽⁴⁾

Refernces

Synthesis of hydroxyquinoline derivatives, amino-hydroxychromene, aminocoumarin and their anti-bacterial activities

10.3987/com-04-10089

The research focuses on the synthesis and antimicrobial activity evaluation of various heterocyclic compounds. The study involves the creation of new diaminochromenes, aminohydroxychromene, aminocoumarin, and hydroxyquinoline derivatives through Michael addition reactions using different substituted aminonaphthol, aminophenol, resorcinol derivatives, chloronaphthol, and 4-hydroxycoumarin with α-cyanocinnamonitriles and ethyl α-cyanocinnamates. Specific chemicals like triethyl orthoformate and hydrazine hydrate are also used in the synthesis process to achieve desired products. The newly synthesized compounds are characterized by spectroscopic data (IR, 1H NMR, 13C NMR, and EMS) and tested for their antimicrobial activities against various bacterial strains, with some showing activity against Staphylococcus aureus.

Benzylidenemalononitrile compounds as activators of cell resistance to oxidative stress and modulators of multiple signaling pathways. A structure-activity relationship study

10.1016/j.bcp.2011.05.028

The research, titled "Benzylidenemalononitrile compounds as activators of cell resistance to oxidative stress and modulators of multiple signaling pathways: A structure–activity relationship study," investigates the structure–activity relationship of benzylidenemalononitrile (BMN) compounds and their capacity to induce heme oxygenase-1 (HO-1) gene expression, activate upstream signaling pathways, and protect cells against oxidative stress. The study used U937 human monocytic cells and examined 49 BMNs and related compounds. Key findings include the discovery that electron-withdrawing groups (NO2, CN, halogens) and double meta MeO substituents in BMN molecules increase HO-1 gene induction, while electron-donating groups (OH, MeO, N-morpholino) significantly decrease it. The study also revealed that the activation of c-Jun, Nrf2, p38 MAPK, and p70S6K correlated with specific substitution patterns in the BMN structure. Furthermore, BMN-dependent maximal up-regulation of HO-1 required a parallel increase in Nrf2 and phospho-c-Jun cellular levels. The research concludes that BMNs induce the expression of protective genes by alkylating sensitive cysteine residues of regulatory factors, providing insights into their potential as therapeutic agents for conditions involving oxidative stress.